Vacation Rentals & Homes in Sag Harbor

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148 homes

Beech Tree Cottage

Sag Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“The cottage experience was relaxing and peaceful with a short wa” Enchanting cottage, very comfortable, enjoyed a little interaction with the owner's family and dog. Very sweet.

Price per night from

$684

East Hampton/Sag Harbor Village Fringe

Sag Harbor house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Price per night from

$3,419

Price per night from

$981

Sag Harbor Village Fringe, Great Location

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$2,280

Hampton's Paradise sag Harbor, Southampton

Sag Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,140

Village traditional on a quiet cul de sac

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,270

Beautiful Guest House Waits For You - Hamptons - Sag Harbor

Sag Harbor guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$451

The Seashell House

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$969

no longer avail property Sold !

Sag Harbor cottage

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,026

Great 4 bedroom family home walking distance to the beach and village

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,368

Why Share? Beautiful guest house! Hamptons - Sag Harbor

Sag Harbor guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 38 minutes

Price per night from

$399

Great rentals within 20 miles that match your search

1200ft2 - Great Hamptons location

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$1,140

Very Private and Tranquil House in wooded estate.

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,140

East Hampton Classic

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$1,140

Brand New Southampton Condo

Southampton condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$489

Summer in a Hamptons Cottage

Bridgehampton house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$489

Price per night from

$1,954

A One Of A Kind Beach Vacation Rental

Montauk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$1,026

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$2,508

Romantic Getaway in Southampton (private room/bathroom)

Southampton private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$354

Airy, Woodsy, Walk to Beach, New Saltwater Pool!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$1,059

Charmimg Beach cottage in Sagaponack

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$652

Relax at our East Hampton home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$896

Montauk Royal Atlantic Beach Resort

Montauk condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$570

Mint Southampton Village 5-BR South of the Highway w Heated Pool

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Price per night from

$1,710

East Hampton Summer Rental

East Hampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,140

Architect Designed Home in Waterfront Village

Greenport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$407

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,710

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$428

Fantasy Bay Front Country French Villa

Southampton villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$2,280

Hip & Stylish East Hampton Getaway

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Airy & beautiful home!” We had a wonderful stay at this beautiful East Hampton home. The floor plan is open and makes for an easy flow between the airy living space and kitchen and dining area. The bedrooms are large and well appointed with comfortable beds and fresh linens. The setting of the house is on a wooded acre with incredible views out over the trees and the swimming pool below. The huge deck affords an outdoor dining area perfect for summer entertaining. We will definitely be back for another visit to this amazing get away.

Price per night from

$896

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$1,653

Majestic Southampton Waterfront Estate

Southampton villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

“Incredible home” This was the perfect home for my husband, kids and grandkids. I can't begin to describe how incredible this home was. From the amazing outdoor kitchen, magnificent landscaping, the toasty warm huge pool, with seating enough for our supersized family of 20 with 4 grandbabies. This home was able to house us all comfortably. The inside of the house was clean, spacious and beautifully decorated. The high count sheets were a dream to sleep on (cute pun intended). The air conditioning was set to the perfect temperature. Every day all of us lived in the pool and at night enjoyed the gorgeous sunsets over the bay. To say we loved this home is an understatement. We are still all talking about the amazing vacation. The owner was really really nice to deal with and made us feel welcomed.

Responds fast! avg. 3 hours 43 minutes

Price per night from

$1,384

Great Rates in 2019- No Increases In Rates and Over Holiday Weeks

Hampton Bays house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great time in Hamptons” Jackie and al's place is in a great location. Block away from the canal. Minutes away from the beach. Very Nice house. Looking forward to next summer.

Price per night from

$456

Classic Hamptons Home in beautiful Water Mill - Minimum 2 week rental

Water Mill house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 13

Price per night from

$1,710

Price per night from

$775

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 43 minutes

Price per night from

$846

Waterfront Condo C204 at The Cliffside Resort

Greenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$456

Viewing 38 of 148
rentals in Sag Harbor

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About Sag Harbor

Sag Harbor is historic hamlet with a real maritime vibe. If you're hoping to experience a unique culture, a world away from normal life, this quirky little resort is certainly an option for you. FlipKey has a great selection of homes to choose from. Book today to secure your Sag Harbor stay.

About Sag Harbor

Sag Harbor is a small village located in Suffolk County, New York and has an extremely rich history which tourists are still eager to discover to this day. The first settlers arrived in the 1600s, and by the 1800s became one of the busiest ports in the world, still famed for its marine heritage.

Thanks to years of preservation and care, the majority of the architecture from the 18th and 19th centuries still remains, which include the likes of Greek Revival Houses and Victorian homes for the rich.

The area within and around Sag Harbor has a great deal of nature, as well as many endangered species such as the eastern tiger salamander. Nature preserves in Sag Harbor include Barcelona Neck Preserve, Sag Harbor Woods Preserve and Cilli Farm. Here, you may be able to spot mammals such as the white-tailed deer, red fox, eastern coyote, mink and a variety of bat species.

What to do

If you're interested in seeking out the cultural sights of the region, why not visit the Sag Harbor Fire Department Museum? Built in 1833, this building was created due to four severe blazes which broke out in the 1800s. Now, it serves as a museum and displays a wide range of fire equipment and other interesting pieces to view.

There's also the Sag Harbor Whaling and Historical Museum, located in an 1845 building. Here, you can explore displays of marine heritage with boat displays, models and furnishings as well as special exhibits.

If you're looking to see more of the area, you may decide on taking a trip to the local rocky beach known as Foster Memorial Beach. Or, if you're looking for a taste of adventure, the most popular activities here are kayaking and boating out to Long Island. You will enroll in a two-day course which is ideal for beginners.

Top Sea Harbor travel tips

If you're looking to find a cheaper alternative than traveling to Suffolk County by plane, there is a bus which departs from Manhattan and will drop you off at Sag Harbor. The round-trip fare is just $53 per person.

It would be advised to have a car to get around Sag Harbor, due to the remoteness of the town. This would also be advised if you plan on exploring the other local areas or are hoping to venture out further.

The peak season to travel to this particular region is between May-September, so always book far in advance.

Sag Harbor is the idealized quiet town you may have always wished to escape to; especially if you live in a busy city. Here, you can explore history culture and even try your hand at water-sports if you dare... Book your Sag Harbor vacation rental with FlipKey to start your next trip.

Top Destination reviews

Beech Tree Cottage
Loved this place

This is the perfect little getaway for those who wish to avoid the pretentiousness of East Hampton and Southampton and still enjoy everything that the Hamptons has to offer. Best things - very cute little cottage. Good enough space with off-street parking. The ability to walk into Sag Harbor village in a few mins is a massive plus. Stephen and Emma are so nice and great neighbors if there are any issues. Would definitely recommend this place to anyone.see more

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